


Never assume  because it makes an ass out of u and me

by 1234abcd2815



Category: Teen Wolf (TV)
Genre: Anal Fingering, Boys in Skirts, Crossdressing, Danny Mahealani is Part of the Pack, Derek Hale is a Softie, Established Relationship, F/M, Finger Sucking, Fluff and Humor, Hand & Finger Kink, Hand Jobs, M/M, Multi, Panties, Sheriff Stilinski Knows, Stiles Stilinski is a Little Shit, Stiles Stilinski is a Tease, Stripper Stiles Stilinski, Supportive Derek Hale, The Jungle (Teen Wolf), The Pack Being Idiots, The Pack Finds Out
Language: English
Status: Completed
Published: 2021-01-15
Updated: 2021-01-15
Packaged: 2021-03-12 23:21:10
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,072
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28768479
Author URL: https://archiveofourown.org/users/1234abcd2815/pseuds/1234abcd2815
Summary: “WHAT?” They all screeched in unison. He could feel Derek rubbing his back soothingly, he knew that Stiles hadn’t meant to tell them that piece of information.“Uh oh,” Danny said as he lay back on the floor laughing hysterically at Stiles’ misfortune.“I think we need an explanation. What do you think, Stiles?” Lydia said as straight forward as ever.“Yeah, Batman, I want an explanation.” Erica echoed.Or the one where everyone’s in for a shock when they discover not only stiles wears skirts in his free time, but he also is extremely popular at The Jungle where he works. The Sheriff, however came to know of this information before the pack in a very unfortunate and very embarrassing incident that everyone involved wishes they could forget.
Relationships: Allison Argent/Isaac Lahey/Scott McCall, Derek Hale/Stiles Stilinski, Lydia Martin/Jackson Whittemore, Melissa McCall/Sheriff Stilinski, Vernon Boyd/Erica Reyes
Comments: 5
Kudos: 141





	Never assume  because it makes an ass out of u and me

See, Stiles has always been fairly feminine though out his life and he’s always been a very very sexual person, everyone who knows him would know that, but never did the pack ever think stiles would be a _stripper_ at _The Jungle_.

***

The pack lay sprawled out over Derek’s loft. Jackson and Lydia sat together on the love seat as Danny lay on the floor talking up at them. Isaac was laid across Scott and Allison’s laps while they both stroked his hair making him almost fall asleep. Erica and Boyd were sat in the corner making out oblivious to anyone else. It was Saturday evening which somehow has been banked as pack night. The whole pack and more recently the Sheriff and Melissa McCall as well, just spend the night watching movies and bonding with each.

Derek, John and Melissa haven’t arrived yet, as they’re still driving home from work.

A while back, Derek had taken up the Sheriff’s offer of becoming Beacon Hills’ new deputy. He loved his job even if he didn’t need to work due to his family’s insurance after the fire. It made him feel like he had something to do with his life other than sit around the loft all day passing time.

Stiles was still upstairs in Derek’s room not realising the pack had already turned up. They didn’t bother him. There was no point. Derek would be home soon and would call him down.

***

Barely five minutes later, the wolves heard the Camaro pull up outside.

The three of them burst through the door, looking around at the pack lying carelessly on the floor, snacks and popcorn in every direction. Derek rolled his eye not expecting anything more from them.  
“Where’s Stiles?” Derek questioned. An echo of ‘I don’t knows’ and ‘upstairs’ was heard from everyone. “Of course he is.” Derek mumbled.

“Stiles.” He yelled up the spiral staircases. There was no response from the young man. “Stiles! STILES!”

This time appeared at the top of the staircase.

“There’s no need to shout, Sourwolf.” Stiles complain, running down to meet Derek in a warm hug, pecking him on the lips. “How was you day?”

“Eh, nothing interesting, you?” Derek replied.

“I was bored all by myself all day.” He pouted. Derek rolled his eyes at Stiles’ antics.

They moved to sit down with the rest of the pack after greeting each other. When they looked around he saw everyone looking at him with exasperated expressions.

“Uh, w-what? Are you guys okay?” Stiles said extremely confused and what he’d done wrong.

“Y-your wearing a skirt, Stiles.” Scott explained, “Why are you wearing a skirt?” The pack all nodded wondering the same thing. Stiles looked down at himself noticing the pleated skirt (patterned in plaid, obliviously) which rested at the top of his recently shaved, long legs.

He didn’t even realise he was so used to wearing skirts around Derek that it didn’t even cross his mind that the rest of the pack had never seen him in one before.

“Oh yeah!” Stiles chuckled, “Forgot I was wearing this. Give me a second. I’ll go change.” Stiles goes to move back upstairs to change when he he looks back at Scott. “And Scotty, I’m wearing a skirt because I like it. That shouldn’t be a fucking problem for you all.”

They all nodded excepting the response they were given. Once again he moved to make his way to change back.

“No,” Derek whined, like actually _whined_ , “don’t change. It looks so good on you.” He gave Stiles the literal definition of puppy dog eyes, which unfair. He knew Stiles couldn’t resist him. But it did though. It did looked good on him. Amazing in fact and he knew it.

Stiles’ lithe, but unusually curvy body made it sit on his hips and small waist just the way it should. He had legs that went for miles and a perfect bubble butt to top it all off. It was a very short skirt as well. If he bent over he could guarantee that everyone would get a good look at his lacy, white panties that he loved so much.

“Fine, but just because it’s you.”

Derek moved and sat down on the armchair in the centre of the room pulling Stiles down onto his lap with him. Everyone knew that armchair was Derek’s and Derek’s only. That was until him and Stiles got their heads out of their asses and realised they were perfect for each other then Stiles was also allowed in the sacred armchair.

Stiles lay there contently, melting into the heat of Derek’s chest, which was surprisingly comfy despite the bulging muscles. He bathed in the feeling of Derek’s calloused hand running soothingly up and down his smooth, hairless thighs.

Slowly, he ran his hand higher, edging under the hem of the skirt. His hand moved discreetly to his inner thigh where it stilled as he felt the lace and satin that was there in place of his usual boxers.

“These new?” He whispered, lightly kissing Stiles’ neck.

“Mhm,” he mumbled, wiggling his hips back into Derek’s lap knowing exactly the effect of finding him in panties was having on Derek.

“Stop it!” He growled quietly, grabbing Stiles’ hips forcefully trying desperately not to get a boner in a room full of werewolves. He quickly added, “You need to show me these later, okay?”

Stiles smirked victoriously to himself.

***

“When did you even start wearing skirts?” Isaac questioned out of the blue.

Stiles sighed, he just knew the noisy fucks couldn’t just leave it alone. They had just finished the second movie of the night, ‘Captain America the Winter Soldier’ Stiles’ choice, obviously and he thought maybe, just maybe they had let it go, but no. That could never happen.

“I don’t know probably since I got my job a The Jungle.” He blurted out, slightly annoyed one of them brought it up again, before slapping a hand on his forehead and cursing his inability to have a brain to mouth filter.

He’d started stripping at the club around a year ago, only a few months after his eighteenth birthday. He’d kept in touch with drag queens at The Jungle, so when they saw him grinding his ass expertly against a stranger and suggested he stripped at the club. He thought it would be a great idea.

Why not get money for your surprisingly good dancing skills. I mean he did have the hips for it.

Dancing at The Jungle really helped him become less insecure about himself. The ladies also were the ones who gave him advice on how to make Derek his.

But the pack wasn’t meant to know any of that. Only Derek, Danny and unfortunately his Dad.

It wasn’t that he was ashamed, because he definitely wasn’t, but he didn’t want to answer all their intrusive questions and have Scott stare at him like an alien and Jackson to laugh at him. I guess he’s going to have to deal with it all now though.

“WHAT?” They all screeched in unison. He could feel Derek rubbing his back soothingly, he knew that Stiles hadn’t meant to tell them that piece of information.

“Uh oh,” Danny said as he lay back on the floor laughing hysterically at Stiles’ misfortune.

“You know about this?” Jackson asked his best friend incredulously to which Danny just shrugged at.

“I think we need an explanation. What do you think, Stiles?” Lydia said as straight forward as ever.

“Yeah, Batman, I want an explanation.” Erica echoed.

He sighed heavily, “Well I suppose I have to now,” he shifted slightly on Derek’s lap trying to get comfortable. “Don’t judge me though because frankly it’s none of your business.” He gave Jackson a pointed look aiming the last sentence at him. He replied by raising his hands in mock surrender.

“I work as a stripper at The Jungle and I have done for a year or so...” he finished awkwardly not really sure what else to say.

The pack stared at him with their jaws on the floor. Derek nuzzled into the back of his neck in attempt to comfort him and he watched as his dad dropped his head into his hands groaning at the fact he was hearing about his son’s work again.

“I don’t believe it.” Jackson stated, breaking the silence. Everyone turned to stare at him, “I’m sorry but I just know there is no way that Stiles could be a stripper with how clumsy he is.” Boyd simply leans forward and whacks him over the back of his head at his unnecessary comment.

Shocking everyone it was Derek who spoke next, “Well believe it, he’s amazing at it and super popular over there as well!”

“Your okay with this?” Scott asked Derek. Stiles glares at him scowling. He can’t help but feel offended by the way Scott seemed so shocked that his boyfriend actually supports him. Like what the fuck.

“Yes I’m okay with this, I can’t believe you’d think I wouldn’t be. I don’t control him. Our only agreement is that when he’s work I go with him to sit in the crowd and make sure all the horny motherfuckers are playing by the rules.”

Stiles turned around kissing him lovingly, so glad he has such a caring boyfriend.

“Did you know about this?” Scott was now talking directly to my dad. Why, just why did he have to talk to my dad about this.

“Uh...yeah. Unfortunately I do know about this. I know way to much about this.” He responded solemnly. Jesus Christ. This is about to get a million times more awkward.

“What do you mean ‘to much’?” Seriously, he wishes Scott would just shut the hell up. And they say Stiles is the one who doesn’t know when to stop talking.

“He means,” Stiles starts, quite clearly embarrassed, “that he’s seem me working... In person” he finishes looking down at the floor his cheeks burning red.

“I didn’t think strip clubs would be your scene, Sheriff.” Lydia says looking somewhere between disturbed and interested with this whole situation.

“NO! I wasn’t there because I wanted to be. It was just a bar fight needing to be broken up and the police ended up being call. I was there for work. Not because I wanted to be. Not at all” he said quickly correcting Lydia’s assumptions. “It was...quite traumatic to say the least. I mean he constantly goes on about trying to save me from having a heart attack, but what was he expecting when I look over to see my own son on stage half naked.”

“Oh my god, dad. Please, _please_ can we not talk about it. It was traumatic for me too.” Stiles didn’t think he could be anymore humiliated right now. He refused to even look at his dad, but he knew that he would be just as red in the face as Stiles is.

It honestly was traumatising.

He had been having a really good night. The tips were high and he was feeling really confident in himself.

That was until he spotted his own dad in the busy crowd gaping at him.

He didn’t even know what to do. He stumbled slightly trying to get over shock quickly and keep the show going.

He felt panic rising in him as he continued to roll his hip seductively making the crowd chuck more money on stage. Attempting to stick it down his little panties shorts. They weren’t the most revealing underwear he could be wearing but they still didn’t conceal much.

The conversation he had with his father afterwards was by far the most awkward part.

In the end they both agreed to never mention it again. Stiles was an adult now and it was his decision.

Well, so much for never speaking of it again.

He focused back on what was happening in the loft after his vivid flashback that horrific night. Most of the pack was laughing now. It was nice to know that someone was enjoying this.

“So what? You give people lap dances as well?” Jackson said looking at him with a smug look on his face.

“If you want a lap dance, Jackson just ask.” Stiles smirked at him, giving him a wink. To his surprise Jackson looked down blushing. That’s interesting, Stiles wondered. “To answer your question though. Yes I do give people lap dances but only if they offer enough money.”

***

It went on like this for the rest on the night. The pack continued to ask him questions about whether he gives people private dances and how much money he makes in one night. Stiles hadn’t look at his dad all night.

Once they had all trailed out of the loft to go back to their own houses Stiles turned to Derek. He had planned on staying there tonight, to be honest at this point he was pretty much living at Derek’s, most of his stuff was here and he slept over most nights.

He turned in Derek’s lap to straddle him. He gave an exhausted sigh and fell into his awaiting arms.

“Well...that was an eventful evening.” He said hand rubbing up and down Stiles back comfortingly. “You alright?”

“Yeah. Yeah, I’m not going to lie it actually went better than I thought it would. I thought they’d all judge me for it.” Stiles buried his head into Derek’s neck as he spoke making it muffled, but Derek being a werewolf he heard him perfectly.

“Thank you.” He said suddenly lifting his head staring into Derek’s eyes adoringly.

“What for?” Derek asked tilting his head just like a puppy.

“For being you. So many people wouldn’t support what I do, but you, your so kind and you always make sure I’m okay no matter what and you handled the pack perfectly tonight.” Stiles told him honestly, wrapping his arms around Derek’s neck and running his fingers thought his black hair.

Derek smiled sweetly leaning forward and pressing his lips lightly to Stiles’. Before even having a chance to pull away Stiles pressed his lip back aggressively kissing him with as much passion as he could muster.

“I’ve had a long day and I really need to relax,” Stiles whispered seductively against his lips, “think you can help me out?”

“Well if I do remember correctly I was promised a show of those panties.” He squeezed ass suddenly drawing a sharp moan from Stiles’ throat.

Without a word Stiles stood up and rid his shirt before slowly and teasingly he inched his skirt down his thighs. The white fabric peaking through more and more each time until they were entirely visible.

Derek breath hitched as he saw his boyfriend standing in the middle of the room clad in only lace panties.

“Do a spin for me,” Derek’s voice was hoarse much deeper that earlier and his eyes were clouded with lust.

Taking his time Stiles slowly spun until his ass was facing Derek.

“Shit!” He heard him gasp and Stiles smirked knowingly.

The back side of the his panties had a heart shaped hole over his ass with a thin strip of fabric running through the middle only just covering his hole.

“You like?” Stiles questioned as if he didn’t already know the answer.

“You know I do. Now come here,” Derek said patting his lap. Stiles stalked over to him swinging his legs over Derek’s jean clad thighs. He smashed his mouth back on Derek’s gasping and whining as he did so. Derek took this opportunity to lick into his mouth. Stiles rolled his hips down on Derek’s bulging erection.

Derek kissed along Stiles’ jaw and down his neck sucking and biting harshly. There would definitely be hickeys there in the morning. He breathed in the scent of Stiles. The scent of arousal and want.

Stiles ground his hips wildly into Derek’s moaning openly as he did so. It seriously shouldn’t turn him on so much being practically naked next to a fully clothed Derek, but it really did.

“Please,” Stiles begged rutting his hips into Derek while looking him in the eyes.

“Please, what, baby? What do you need?” Derek teased, knowing exactly what Stiles needed.

“Ugh, y-your fingers, please.”

“Your gonna need to get them wet first, baby” Derek stated, shoving his fingers into Stiles’ awaiting mouth.

He swirled his tongue around the digits maintaining eye contact. His sucked like he would suck Derek’s cock knowing full well what effect he was having on the older man.

“That’s enough now” Derek said pulling them from his plump lips watching the shiny silva as it dragged from Stiles’ mouth before reaching behind Stiles and slipping them beneath his panties and rubbing them sensually around his rim.

“Holy shit!” Stiles breathed as he felt the first digit slip past his ring. Derek pumped his finger in and out quickly. They’ve done this enough time now, that he knows exactly where that special bundle of nerves that makes Stiles’ body light up in sparks is.

He slipped in a second and then a third soon after. He hit his prostate with every hard thrust of his fingers

Stiles lay his head on Derek’s shoulder breathing rapidly moaning wantonly every few seconds. Pre-come was leaking through his panties like a waterfall.

“Please, Derek. Please make me cum.” He pleaded.

“Okay, baby.” He said kissing Stiles sweetly on the lips, pulling Stiles’ panties down and letting his cock slap lewdly against his toned stomach. He the unzipped his jeans and dragged his thick uncut cock out from the confined space of his boxers.

He wrapped his large hand around both their cocks and stroked them quickly using their pre-come as lube, while continuing to put pressure on Stiles’ prostate.

Before long he felt Stiles’ thighs begin to shake and he knew he was about cum.

“Fuck!” Stiles moaned loudly, quivering and cumming over Derek’s hand. Only a tug later and Derek was cumming with him.

Once they had both gained their breath back Derek lifted his cum covered hand to Stiles’ mouth and watched as he lick it clean.

His cock twitched slightly at the sight but it was far to soon for another round.

“I love you.” He whispered in Stiles’ ear.

Stiles lifted his head to kiss Derek lightly, “I love you too, Sourwolf.”

**Author's Note:**

> This is actually my first work that I’ve ever written and I would really appreciate and kudos and/or comments. Constructive criticism is very welcome as I would love to improve in any way for future writing


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